Hands-on startup advice for emerging entrepreneurs

A version of this article previously appeared in Forbes. Self-aware startups often learn more from their failures than from their success. Timehop, the photo album for the digital age, is no exception. Created by Jonathan Wegener and his Co-Founder Benny Wong, the company has over 16M+ users. To put this in proper perspective, more than twice as many people access Timehop each day than read the New York Times. And Then The CEO Said, “Go Home” Timehop recently executed a radical experiment. With winter raging outside, it closed its NYC office for two weeks and made all of its employees work remotely, preferably not from their homes. Many of the employees took off for exotic, sun-drenched locales.

A version of this article previously appeared in Forbes. When joining a startup, there are seven important questions you should ask in order to answer the question: “What the heck are my stock options worth?” You just received a job offer from a startup which includes 50,000 stock options. That is wonderful…or is it? I reviewed and approved hundreds of employment offer letters at my various startups, all of which included stock option grants. The number of otherwise intelligent prospective employees who never ask relevant questions about their stock options was frankly shocking.

A version of this article previously appeared on Forbes. The US Postal Service pulled off another debacle with the Maya Angelou stamp. Their task was simple. Combine a photo of Ms. Angelou with one of her more memorable verses. Instead, the coupled her image with text written by Joan Walsh Anglund.

A version of this article previously appeared in Forbes. Young Al Kooper did not miss his Bob Dylan moment. When Al was invited by Producer Tom Wilson to sit in on Dylan’s Highway 61 Revisited, Mr. Wilson made it clear to Al that he was a backup guitarist. He told him to sit quietly in the control booth and be ready to play if Dylan wanted to explore an arrangement that required two guitars. According to Al, “Me being twenty one years of age and very ambitious… I decided I was going to play on that session.” However, it was quickly evident to Al that his services wouldn’t be needed, as Dylan’s primary guitarist was Mike Bloomfield, a more experienced and proficient musician.

A version of this article previously appeared in Forbes. In this second installment of my conversation with George Powell, Founder and President of Skate One, he describes how Tony Hawk and the other members of the Bones Brigade revolutionized skateboarding and made it cool again, after its near death in the late-1980’s. He also shares his frank thoughts regarding his long-standing relationship with Stacy Peralta. Skate One is now the world’s largest skateboard company, with best-selling brands such as Powell•Peralta Skateboards, BONES Wheels and Mini•Logo Skateboards. You can read part one of our discussion here, which covers a number of insightful topics, including the origin of Skate One and George’s multi-decade partnership with Stacy Peralta.

A version of this article previously appeared in the Wall Street Journal. You have been planning to ask your long-time partner to marry you for months and the big day has finally arrived. In order to reduce your risk of failure, you ask your roommate, who has proposed to several times previously, to pop the question on your behalf. Sound crazy? This is the approach many startups take when they communicate their story to the market. Rather than directly explaining their value proposition with all the passion and heartfelt stridency that only an entrepreneur can deliver, they outsource this communication to a Public Relations (PR) firm. PR agencies are expensive versions of Cyrano de Bergerac. Their best attempts to woo the media will never equal your ability to sing your own praises.

A version of this article previously appeared in the Wall Street Journal. Avoid a simple pricing mistake which could sink your startup. The “D” word - Discounts. I buy my cars in December. Why? Because I am cheap and I know that car dealers are incentivized by the manufacturer to hit quarterly and annual sales goals. The rewards are in the form of co-marketing dollars and commission spiffs. Thus, the value of a sale at the end of a quarter can be significant, if the sale contributes to obtaining a manufacturer's incentive. Individual salespeople are commissioned in a similar manner, based on attaining monthly and quarterly goals. If selling one more car at the end of a quarter will earn a sales rep a trip to Hawaii, they may be willing to forgo most or all of their commission to get the sale.

A version of this article previously appeared on Forbes. George Powell is proof that you can do well by having fun. Rare and fortunate is the person who successfully converts their passions into a lucrative vocation. Mr. Powell, Founder and President of Skate One is such a man. The world’s largest skateboard company, Skate One produces many of industry’s best-selling brands, including Powell•Peralta Skateboards, BONES Wheels and Mini•Logo Skateboards. I am always on the lookout for inspiring entrepreneurs who have leveraged their passions into healthy livelihoods as they serve as instructive role models for my UC Santa Barbara entrepreneurial students. After speaking with Mr. Powell, it was clear he fit the bill. This is the first of a two part, extensive interview I recently conducted with Mr. Powell.

A version of this article previously appeared on Forbes. Raising too much cash, too early, can kill your startup. It can provoke spending on unproven business models, hiring employees before their talents can be fully tapped and entering into long-term, unsustainable relationships with partners, landlords and other third parties. To avoid these death knell mistakes, create a culture in which you and your employees (your CFO excepted) spend your precious cash with zero regard for how much money you have in the bank. Sound counterintuitive? Hardly. Startups should only spend their money on initiatives that deliver a discernible, measurable return on investment.

A version of this article previously appeared in the Wall Street Journal. “You miss 100% of the shots you never take.” Wayne Gretzky Imagine how difficult it would be to score in hockey if you were required to rely on someone who is not your teammate to convince another third-party, whom you have not met, to take a shot on your behalf. As crazy as this scenario sounds, it is very similar to the “scoring process” companies engage in when they track Net Promoter Scores.